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Straightforward Access to 3,4‐Dihydro‐2 H ‐1,2,4‐benzothiadiazine 1,1‐dioxides and Quinazolines via Iron‐Catalyzed Aerobic Oxidative Condensation of Amines
Author(s) -
Gopalaiah Kovuru,
Tiwari Ankit,
Choudhary Renu,
Mahiya Kuldeep
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900850
Subject(s) - benzothiadiazine , chemistry , benzylamine , oxidative phosphorylation , combinatorial chemistry , condensation , catalysis , quinazoline , organic chemistry , biochemistry , physics , thermodynamics
A novel and straightforward approach for constructing 3,4‐dihydro‐2 H ‐1,2,4‐benzothiadiazine 1,1‐dioxides from 2‐aminobenzenesulfonamide and benzylamines via oxidative condensation has been explored. Abundant and cheap iron salt as a catalyst and air as an oxidant were employed, which makes the process more practical and economical. This reaction protocol was further applied to synthesize diverse functionalized quinazolines through oxidative condensation of 2‐aminobenzylamines with benzylamines. Besides this, the use of amino acid such as phenylglycine as benzylamine surrogate has also been tested for the construction of 3,4‐dihydro‐2 H ‐1,2,4‐benzothiadiazine 1,1‐dioxide and quinazoline derivatives. The proposed mechanistic pathway has been validated by isolating the key intermediates.